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Chloroacetone → 1-(4-{1-[3-(Trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenoxy)propan-2-one

HRID 2381146
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인쇄 미리보기

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HRID 2381146 반응식
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:32])([F:31])[C:9]1[N:13]2[N:14]=[C:15]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=4)[CH2:20][CH2:19]3)[CH2:16][CH2:17][C:12]2=[N:11][N:10]=1.Cl[CH2:34][C:35](=[O:37])[CH3:36]>CC(N(C)C)=O>[F:32][C:8]([F:7])([F:31])[C:9]1[N:13]2[N:14]=[C:15]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[CH:25]=[CH:26][C:27]([O:30][CH2:34][C:35](=[O:37])[CH3:36])=[CH:28][CH:29]=4)[CH2:20][CH2:19]3)[CH2:16][CH2:17][C:12]2=[N:11][N:10]=1
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참가 물질

5

반응물 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 685004304-{1-[3-(Trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenol

생성물 1

HCID 684994251-(4-{1-[3-(Trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenoxy)propan-2-one수율 96.4%

시약·촉매·용매 1

HCID 31374
Dimethylacetamide
용매

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온도
100 °C

실험 절차

Potassium carbonate (1.214 g, 8.79 mmol) was added to 4-{1-[3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenol (obtained as described in Example 46, preparation of starting materials) (1.07 g, 2.93 mmol) and 1-chloropropan-2-one (0.466 mL, 5.86 mmol) in DMA (10 mL). The resulting mixture was stirred at 100° C. for 2 hours. The reaction mixture was cooled to room temperature, concentrated and diluted with water (25 mL) then extracted with DCM (2×25 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 50 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 1-(4-{1-[3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenoxy)propan-2-one (1.190 g, 96%) as a gum.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additiondiluted with water (25 mL)
  4. extractionthen extracted with DCM (2×25 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto afford crude product
  9. customThe crude product was purified by flash silica chromatography, elution gradient 50 to 100% EtOAc in isohexane
  10. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-f2f1b38ca12346d182bda33bcd90716c
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08258140B2

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